If you’ve watched Barbara Corcoran on Shark Tank or listened to her advice on her new podcast, Business Unusual, you pretty much know what to expect with this real estate mogul: 100%, unfiltered, no-BS honesty. But spend an hour with her at her brightly-painted and cheery office on Park Ave. in NYC and you’ll see how much grit she really has. She’s gone through career defeat, she’s had her own failures, she had to make a name for herself in the male-dominated field of real estate, and she’s let none of it get her down. Over wraps and soup, I chatted with Barbara about overcoming self-pity, the importance of making time with friends and the need for apps like VINA to meet the girlfriends who will impact your life for the better and so much more.

Read our full Q&A below, and be sure to check out our video for more with Barbara!

VINA: After your early career success, you could have sat back and enjoyed the ride, but you have found so many outlets to help others—your book, Shark Tank and your podcast, Business Unusual. Why was it so important for you to share your intel with aspiring entrepreneurs?
BC: Anything I can do to help my sisters, I’m all for.

VINA: When you look back on your career path, you have talked about never making excuses for any challenge or obstacle thrown your way. We see a lot of our community sometimes struggling with negative self-talk and feeling powerless about their situation at times. What do you suggest can they start telling themselves when things don’t go as planned?
BC: I feel very strongly about this and I can answer very honestly and it’s probably what you need to hear, anyway. I think that women have to label discouragement as self-pity. And once you do that, you declare it the enemy. So I’ll feel sorry for myself for a second or I’ll feel the downside of a rejection, but I immediately see it for what it is: I’m gonna feel sorry for myself just because of a little bump here? So I get myself out of that position right away. Because what happens is you can easily get in a rut of negative self-talk, negative self-pity. But I label it as an enemy because I see it as an exact equivalent of giving your power away.

Many do negative self-talk as a whole reel in your head, and we’re very capable of changing our own reels — I’m totally sure of that because I’ve had to do it. If I can do it, the next guy can do it. It’s just a matter of persisting and knowing that you’re in charge. Then what happens is you take your power back.

I don’t like the idea of giving my power away for even three minutes. I take it back, and how do you take it back? You decide you have to do something about it. I do it because I have learned that’s what it’s all about. I hate to make it sound so simple but — not just with women, but the men I work with, my partners, my employees over my life, my ladies here…if anything goes wrong, if I see them licking their wounds just for a second, I’m like, “Nope. Now what are we gonna do about it?” You can always do something about everything. Everything bad you can do something about. And then you get the phenomenal reward that I’ve learned my whole life is the worst belly-flops always have the biggest upsides. Like a bouncing a ball on the ground, the harder you hit, the better it bounces it up, you can grab a high ball. But unless you’re willing to stand up and get ready for that ball coming back up, you’re going to miss that whole bounce.

VINA: In your podcast, you answer listener-submitted questions. What are some unexpected trends you’ve noticed?
BC: People ill-content with their position in life. I feel like everybody I talk to is ill-content, wondering if they should be in business for themselves or if they should be asking for the raise, wondering if they should be aggressively pursuing the job that they really want but are afraid to leave the old job.

VINA: You famously had 22 jobs before you started your real estate company at age 23. If someone wants to switch tracks and find their perfect career, what is your best advice?
BC: You know, I think a lot of people think they have to go from A to Z; no, I think all you have to do is get the first step. It’s much like exercising in the morning — I’m always exercising, I hate it every single day, but I break it down for myself to allow myself to do it. It’s the same kind of thing. I just stare at my sneakers by my bed — if they’re in my closet I won’t get up, I know myself — if they’re by my bed, all I have to do is get one foot in one sneaker and somehow you get that foot in and you’re out the door. Apply that to the job front, all you really have to do is go online and see what’s out there. All you really have to do is update your resume. All you really have to do is take a new picture to put up since everybody is checking your profile before they interview you, hopefully.  All you have to do is take the first baby step — you can’t get momentum by sitting still. You can’t get momentum by thinking, and if you’re going to analyze what the right thing to do is, you’re never going to move. You just have to get it going. Any little old baby step will get you going, get some momentum going forward. I think that’s the best advice for people; just get going and see how you feel, see what you think. Just take your first step, it’s so satisfying and you know what? Even if you stumble on your first step, the pride and self-confidence you get from making a step is worth it. It just makes you feel good about yourself. Like any first step, just in the right direction.

VINA: We hear a lot about how important it is to have happiness in your workplace and actually enjoy where you work. If you’re a boss or a manager, what can you do to help make your employees happier?
BC: You can create your environment from the color of the walls, to the hours, to the vacations, to the pay, to the bonuses and surprise bonuses, to the compliments, to the award systems established, to the pure unadulterated attention to detail that’s going to make anyone happy, and everybody’s capable of figuring that out. I think you have to have the desire to have a happy family. It’s something not on a lot of people’s radars in business, which is amazing to me, because even the greediest, cheapest guy in the world who doesn’t create a great environment is an asshole, frankly, because he’s losing money.

I’ve watched the difference, I’ve moved to a new office and made it like a spa, made it a beautiful place to work, and I watched my commission pop up immediately. And the rent I didn’t think I could afford was easily covered. So I think you have to get dedicated to pushing off a portion of your time as a boss to create fun in the workplace, to create fun outside-the-workplace.

My best day last week was when I forced all these kids — after two weeks of saying you’ve got to see the new Queen movie (Bohemian Rhapsody), I’ve seen it three times and I’ve never seen a movie more than once in my life. After two weeks of saying you’ve gotta go out and see it, they didn’t go out. I mean, they have their own life on the weekends. So I came in on Monday morning, I bought three tickets, they went to the movies, I said don’t come back, go out for lunch and the movies. They loved it. Who got the best work from their employees? Me? Of course I did. Did I do it for that purpose? Truthfully, halfway. But I really wanted them to see that movie. It was so deliciously motivational, good, intriguing, educational. What doesn’t it have? You’re a loser if you don’t see it, frankly.

You’ve put money in the bank for the future, no matter how you look at it. You get your biggest bang for your fun buck in business. I have no doubt — you get creative force, you get teamwork, you get love, that feels good, right? But it’s the most underutilized part of business, fun. And it’s so silly, it’s so profitable, really. Who doesn’t want to be happy at work? And do you know, I can actually brag — I’ve never lost an employee, and I’ve employed thousands of people in my life. Never has anyone left unless I told them to leave, which I did a lot. People, if they’re happy at work, they do not leave.

VINA: Your 20s were extremely busy–you were running a highly successful real estate company in NYC. You wrote in your book of the nights you just collapsed into bed, barely sleeping. As Hey! VINA is a friend-finding app, we have to ask–did you make time for friendships? Why or why not?
BC: Well, I’ve always had girlfriends and they’re my best asset today, girlfriends. I mean, what would you do without girlfriends? I’ve had two husbands — I’m still with Bill 38 years later, it’s shocking… but here we are! Two peas in a pod! With the girlfriends, I have the longest range girlfriends from — you know what happens, you meet your best friends when you’re young, I really believe that. You meet your lifelong friends when you’re young. Two categories: your early job experience, you get your best friends. They’re different than the friends you have any other time. And when your kids are young, you make a second group of best friends. After that, you’ll never make best friends like that again.

I’m very friendly, I make friends so easily really, because I really like people, and I have so many friends — but they can never compete with my original girl friends through those two sectors of my life. They’re my best buds. So lucky for me, as hard as I worked, I always had a couple of girl friends from that, and then I got five or six good girl friends from the children’s years, but in the end, I really have two friends, that’s how I figure. Two closest, bosom buddy friends. One’s 10 years older than me, one’s 10 years younger.

VINA: What were you looking for quality wise when you were young?
BC: My first qualifier is, “Do they have a sense of humor?” And I use that to choose friends today. The sense of humor for me is number one. They don’t have a sense of humor? They’re not my friend. I had a Scrabble party last night with eight Scrabble friends. I realized we were sitting there, we were laughing and laughing and laughing, I realized every single one of my Scrabble friends — because I have a lot more people that want to play Scrabble — but they’re all funny people. They laugh, they enjoy life. And that’s who you want to be around.

Okay, the other quality, I would say big-hearted. Big-hearted is so undervalued. You get a big-hearted friend, a cluster of great attributes come with them. They’re generous with their time, with their emotions, with their limited resources they want to share naturally, they’re kindly to you and the people you love. They’re not gossipers, they’re not negative. Big heartedness is a big one. My friend Edie, she’s 6 ft. 1 from Berlin, she’s big, tall, oh she’s scary. But you know, you look at her, and all I can see is her heart is five times taller than her height. She’s got the biggest heart! Edie would do anything for any Joe off the street, nevermind me, and I’m her best friend. How lucky am I? My friend Lizzie, I mean, she would take the shirt off her back — when she’s not drinking too much wine. And my gay friends qualify as my girlfriends, by the way. I do have four very good gay male friends.

Barbara Corcoran, Brittany Galla, Olivia June

VINA: You know the saying “The road to success is often a lonely one.” Did you ever feel lonely during that time? Do you agree with that notion? 
BC: I never did, but you have to remember that I had Ramone Simone, who gave me the $1,000 and he was my business partner, so I had that camaraderie of having a partner in the business. And then when he left me, I made Esther Kaplan my partner, and so I had Esther who was always with me, had my back. She’s a 10 percent partner, you might say that’s not enough but it certainly is, she’s my partner, we planned everything together. I also had a huge family. I was really the mom [of my siblings]. No doubt I was the mom. I loved my kids the way you love kids — my salespeople, my staff. I did anything in the world, I’d spoil them rotten, I’d kill for them, and they would kill for me. So how do you feel lonely in a big happy family, you know? So no, I don’t really feel like I ever felt that way.

VINA: When you were in real estate, it was very much a male-dominated field, as basically all business is. How challenging was that for you?
BC: Huge advantage being the only woman in my field. Huge! I know it’s valid, certainly in the corporate environment to say “oh, the women don’t –” But let me tell you, when you’re in business for yourself, it is not a disadvantage to be a female. And if you’re in a male-dominated business, it’s a huge advantage. I played that card over and over and over again. Everywhere I could, I wore hot pink suits, bright red suits, I had short skirts, I had good legs, I flirted unabashedly with the men because they fall for that shit. Women don’t fall for that. You say, “You’ve gotta be one of the most handsome guys I’ve ever met in my life.” A guy who’s average will agree with you. You say that to a women, she says, “Who’s she? Who’s she kidding?” Because women are smarter, right? It was a great advantage, and you didn’t even need to be remembered. I didn’t care if they knew my name. It’s just “Oh, the woman.” I was the only one. Imagine if I’d had five women competing with me. I couldn’t have had that handle right away. Great advantage. Lucky me. It was an advantage until Lori [Greiner] came on the Shark Tank set. I was the only woman.

VINA: Are there any products or service that you wish existed for women but nobody has created yet?
BC: Invented for women…yes. Let’s think. An excuse book: “But Not Tonight Dear.” Okay, I have the best excuses in the world. Multiple ones, but I ran out probably 10 years ago and now my husband’s pretty much seen through them all. Like, “Is that a cold sore?” “You don’t have a cold sore, Barbara.” He used to fall for that again and again and again!  I would like a big fat book of excuses to avoid sex after you’ve been married 10 years. I only have like a dozen.

VINA: What do you think is the #1 pressing issue in the world today that could be feasibly be fixed in the next 10 years?
Besides politics, I would say technology robs people of so much stuff. Finding a balance there I feel is almost an impossibility. But I feel like I lose — I work very hard not to have technology overtake me, or information overtake me. I shouldn’t say technology, it’s the phone, the goddamn phone, you know? Texts, photos, need for decisions on emails, emails, more emails, copies of emails, things I shouldn’t be copied on. I have five sisters and everything that every sister puts out to one sister copies the rest of us. It’s endless, you cannot keep on top of it. Why I find it difficult — I’m a very neat person, I like to finish things up and I’m very organized, I like a clean closet before I go to bed. That’s the closet that never gets clean, it’s a nightmare. No matter how hard you try, you can never catch up to that closet. And that gives me great anxiety. And so finding a balance there, staying informed, being responsive, making people feel important, it’s all happening through the phone today.

I don’t want to sound like an old person — but I personally don’t have enough quality time having conversations with people. I put a stick in the sand a couple weeks ago — I decided I was going to call one sister every Sunday to have a conversation because I realized I didn’t have a physical conversation with any of them for almost two years now. We text like crazy, but we don’t have a conversation. And my other rule I made a year ago, which I’ve been setting to — if I get a text more than one, two, comes back a third time, I pick up the phone and call. Because that’s a visit. A text is not a visit. And yet, 90 percent of all our relationships are by texts today.

A text is not a visit. And yet, 90 percent of all our relationships are by texts today.

I called my favorite sister, my baby sister, twice, two Sundays in a row. You know what she said when I called a second time? She said, “Barbara? Calling again? Twice in one month? Oh, how nice!” And I felt like crying, honestly. I love her dearly, but all we do is text. And I found out so much of what was going on — it was a visit. You can visit by telephone but you can’t do it by text, that’s what I’ve concluded.

VINA: How do you make time for your girl friends, too?
BC: My friends I see because they’re local, and I am extremely good at putting fun first there, so I make dates with them. So, usually on a Sunday, I look at my next two weeks and say, “Where am I gonna have fun?” So I have tons of dinner parties with friends. My house is party central — I wouldn’t say party-eat-central, I guess, just a bowl of pasta.

I feel lonely when I’m texting, even with my friends. I have a general sense of sadness when I’m texting, even if it’s a happy text, such as, “Hey, happy to hear about your new grandchild, that’s great.” But I feel sad. But you get on the phone, you feel a connection.

VINA: We agree. On VINA, our goal and mission is to encourage women to take their friendships offline and have in real life experiences, so we completely agree with you. That’s why we have 30+ communities for vinas to join, such as New Moms, New in Town, Students, Expats and more.
BC: Oh! That’s great. For making new friends, wow. That’s nice. Especially for women raising kids, those are the loneliest ones.

Start building your girl gang today on the Hey! VINA app. Download, match, make plans and meet up–it’s that easy!